An alkoxybenzene compound and an aryloxybenzene compound are very useful industrially, and, for example, 4-alkoxy-2,5-diacylphenols and 4-aryloxy-2,5-diacylaminophenols recently are attracting attention as a cyan coupler in the field of photographic chemistry [see JP-A ("JP-A" means unexamined published Japanese patent application) Nos. 35731/1985 and 49336/1985 and U.S. Pat. No. 4,579,813].
The alkoxybenzene compound and aryloxybenzene compound having a substituted amino group at the ortho position are quite important intermediates for the synthesis of many industrially useful compounds, such as photographic color mixing inhibitors (e.g., JP-A No. 81341/1988), chelate dyes (J. Org. Chem., 47, 2607 (1982)), and antibacterial agents (J. Med. Chem., 28 24 (1985)).
Also, a variety of applications of the alkoxybenzene compound and the aryloxybenzene compound includes use as a synthesis intermediate from which dyes and physiologically active compounds (e.g., pharmaceuticals and agricultural chemicals) can be derived.
A typical conventional process of synthetically producing these alkoxybenzene compounds and aryloxybenzene compounds is the one represented by the following scheme 1. ##STR1##
In the above scheme, R.sub.11 represents a group that is capable of being substituted onto a benzene ring, R.sub.12 represents an acyl group or the like, R.sub.13 represents an alkyl group or an aryl group, and n is an integer of 0 to 4.
That is, generally, the alkoxybenzene compound or the aryloxybenzene compounds represented by formula (X) are produced by using, as a starting raw material, a phenol compound (III), introducing a nitrogen atom to the ortho position of the phenol by nitration or diazo-coupling, and then carrying out alkylation or amidenation.
In the process of the scheme 1, aniline compound represented by formula (VI) or (VIII) is readily oxidized and colored intensively and thus low in purity in many cases. Under nitration conditions in the process from (III) to (IV), quinone is produced, in many cases, by the oxidation reaction (for example, when a halogen atom or alkoxyl group is present on the benzene ring: see J. Chem. Soc., 1963, 3028; J. Am. Chem. Soc., 71, 3953 (1949); and J. Org. Chem., 4, 555 (1939)). Further, in the synthesis of (VII) from (III) by diazo-coupling, the productivity is low in many cases, since a large amount of solvent is required.
Further, it is quite difficult to convert from (III) to (IV) and from (III) to (VII) selectively with respect to the position.